Mike Reiss has spent over half of his life writing for "The Simpsons." He shares the secrets behind Springfield. Plus, author Ottessa Moshfegh ponders what it would be like to unplug for a year in her novel "My Year of Rest and Relaxation" and io9 blogger Beth Elderkin talks about the history and the allure of the cliffhanger ending.

Pulitzer Prize-winning author Jennifer Egan dives deep with her latest book, “Manhattan Beach.” And, poet and critic Kenneth Goldsmith offers his love letter to the Big Apple. Plus, “Too Many Cooks” creator Casper Kelly is back with another viral video and Nicholas Smith talks about the footprint sneakers have had on American culture.

Amber Ruffin is the pioneering performer and writer for “Late Night with Seth Meyer.” She talks about why her comedy is finding a home in a charged climate. Plus, “Room to Dream” author Kristine McKenna collaborated for a biography/memoir with David Lynch. And, writer Kirk Walker Graves unpacks the significance of Kanye West’s masterpiece “My Beautiful Dark Twisted Fantasy”

Humorist Dana Schwartz has turned her memoir into an interactive reading experience in “Choose Your Own Disaster.” Author Nafissa Thompson-Spires new collection of stories, “Heads Of The Colored People” explores Black Experiences. And UK writer Danny Wallace politely digs into the culture of rudeness and Chuck Klosterman puts on his lab coat for a BETA Rock and Roll Thought Experiment.

Author Carmen Maria Machado fearlessly bends genres in her collection, “Her Body and Other Parties.” Jonathan Lethem honors Talking Heads' 1979 album “Fear of Music.” Video game writer Tom Bissell opens up about the legacy and personal sorrow of "Grand Theft Auto IV" and Tedium’s Ernie Smith offers a brief history of ringtones.

Comedian Scott Thompson revives his iconic and no-nonsense Buddy Cole character just in time. Plus, Paula Poundstone's journey for human happiness and a look back at the cultural touchstone that was They Might Be Giants' "Flood" with S. Alexander Reed.

Stand-up comedian Laurie Kilmartin talks about how the loss of her father inspired her to find the funny side of death. Justin Simien talks about his ambitious, provocative and funny Netflix series, "Dear White People"; and just when you thought it was safe to to take a shower again, we revisit one of the most famous scenes in cinema history -- the shower scene from Alfred Hitchcock's 1960 shocker, "Psycho."

Comedy writer Nell Scovell broke into Hollywood in the eighties by "writing like a man." Now, she's an inspiration and advocate for female comedy writers. Musician Larry Norman was a little too rock-n-roll for the church and a little too Christian for rock, but he never stopped his pursuit of both. Jimmy O. Yang went from being an outsider in Hong Kong, to being an outsider in the US until he pursued his passion of stand-up comedy.

From Stefon to hitman, comedian Bill Hader channels his personal struggles into the HBO comedy/drama "Barry." Can you remember the last time you used a phone booth? Can you remember the last time you saw a phone booth? Author Ariana Kelly explores the phenomenon of phone booths in pop culture. And, author Jonathan Abrams taps into the oral history of "The Wire."

"The Simpsons" has been on TV for nearly 30 years. Comedian Hari Kondabolu feels that after all these years, it may be time to update some of the jokes. Also, a sister shares the heartbreaking story of losing Harris Wittels, a rising star in comedy. And, an exploration into awkwardness with "Cringeworthy" author Melissa Dahl.